US1780860A - Betainethiocyanate - Google Patents
Betainethiocyanate Download PDFInfo
- Publication number
- US1780860A US1780860A US286484A US28648428A US1780860A US 1780860 A US1780860 A US 1780860A US 286484 A US286484 A US 286484A US 28648428 A US28648428 A US 28648428A US 1780860 A US1780860 A US 1780860A
- Authority
- US
- United States
- Prior art keywords
- betaine
- parts
- thiocyanate
- weight
- betainethiocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 20
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 16
- 229960003237 betaine Drugs 0.000 description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960003403 betaine hydrochloride Drugs 0.000 description 2
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal thiocyanates Chemical class 0.000 description 1
- 229940023579 anhydrous betaine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
Definitions
- the present invention relates to the manufacture of betainethiocyanate.
- betaine thiocyanate is obtained by combining betaine (trimethylglycocoll) with thiocyanic acid or by causing decomposition of betaine salts, especially betaine hydrochloride, with suitable salts of the thiocyanic acid, such as ammonium thiocyanate or alkali metal thiocyanates.
- Betaine thiocyanate has valuable advantages over the known compounds of thiocyanic acid used in therapy, since it exerts the pure action of the acid due to the fact that the betaine undergoes complete combustion in the organism and causes a considerable increase in the separation of urea as well as of sodium chloride from the body, which is of value in the case of some diseases.
- Example 1 185 parts by weight of crystalline betaine or 117 parts by Weight of anhydrous betaine are dissolved with stirring in 480 parts by weight of aqueous thiocyanic acid, containing 8.3% of thiocyanic acid; The solution is'cooled, whereupon part of the betaine thiocyanate crystallizes out. Af- I ter filtering from the crystals, the mother liquor is evaporated to a small volume in vacuo at a temperature not exceeding 100 G., cooled and again filtered. By re-crystallization from alcohol or water the betaine thiocyanate is obtained in the form of colorless crystals. The melting point is 167 C. (with decomposition). The process proceeds according to the following equation:
- E trample 51-46 parts by weight of ammonium thiocyanate are dissolved in 150 parts by weight of hot alcohol and the solution is mixed with a hot solution of 153.5 parts by weight of betaine hydrochloride in 150 parts of water.
- the betaine thiocyanate crystallizes out on cooling. Purification is effected as described in Example 2.
- Betaine thiocyanate forming colorless crystals of the melting point 167 C. (with decomposition) and being a product of great therapeutical value.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Patented Nov. 4, 1930 UNITED STATES RUDOLF IBERENDES AND LUDWIG SCHU'TZ,
OF ELBEBFELD, GERMANY, ASSIGNORSTO WINTHROP CHEMICAL COMPANY, INC., OF NEW YORK, N. Y., A CORPORATION OF NEW YORK BETAINETHIOCYANATE No Drawing. Application filed June 18, 1928, Serial No. 286,484, and in Germany June 28, 1927.
The present invention relates to the manufacture of betainethiocyanate.
In accordance with the invention betaine thiocyanate is obtained by combining betaine (trimethylglycocoll) with thiocyanic acid or by causing decomposition of betaine salts, especially betaine hydrochloride, with suitable salts of the thiocyanic acid, such as ammonium thiocyanate or alkali metal thiocyanates.
Betaine thiocyanate has valuable advantages over the known compounds of thiocyanic acid used in therapy, since it exerts the pure action of the acid due to the fact that the betaine undergoes complete combustion in the organism and causes a considerable increase in the separation of urea as well as of sodium chloride from the body, which is of value in the case of some diseases.
The following examples will illustrate our invention, without limiting it thereto:
Example 1.-185 parts by weight of crystalline betaine or 117 parts by Weight of anhydrous betaine are dissolved with stirring in 480 parts by weight of aqueous thiocyanic acid, containing 8.3% of thiocyanic acid; The solution is'cooled, whereupon part of the betaine thiocyanate crystallizes out. Af- I ter filtering from the crystals, the mother liquor is evaporated to a small volume in vacuo at a temperature not exceeding 100 G., cooled and again filtered. By re-crystallization from alcohol or water the betaine thiocyanate is obtained in the form of colorless crystals. The melting point is 167 C. (with decomposition). The process proceeds according to the following equation:
om CH;
CH: 0 Ha Example 2.76 parts by weight of ammonium thiocyanate are dissolved in 33 parts of hot water and the solution is mixed with V a boiling solution of 153.5 parts by weight of cohol or re-crystallizing from water. The process proceeds according to the following equation:
E trample 51-46 parts by weight of ammonium thiocyanate are dissolved in 150 parts by weight of hot alcohol and the solution is mixed with a hot solution of 153.5 parts by weight of betaine hydrochloride in 150 parts of water. The betaine thiocyanate crystallizes out on cooling. Purification is effected as described in Example 2.
We claim:
Betaine thiocyanate, forming colorless crystals of the melting point 167 C. (with decomposition) and being a product of great therapeutical value. c
In testimony whereof we have hereunto set our hands.
RUDOLF BERENDES. [1,. a]
LUDWIG scHu'Tz; a 3.1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1780860X | 1927-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1780860A true US1780860A (en) | 1930-11-04 |
Family
ID=7743001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US286484A Expired - Lifetime US1780860A (en) | 1927-06-28 | 1928-06-18 | Betainethiocyanate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1780860A (en) |
-
1928
- 1928-06-18 US US286484A patent/US1780860A/en not_active Expired - Lifetime
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